Abstract
The compounds, 5-methyl-5H-dibenzo[b,f]azepine (1) and 5-(4-methylbenzyl)-5H-dibenzo[b,f]azepine (2), were synthesized and characterized by spectral studies, and finally confirmed by single crystal X-ray diffraction method. The compound 1 crystallizes in the orthorhombic crystal system in Pca21 space group, having cell parameters a=11.5681 (18) Å, b=11.8958 (18) Å, c=8.0342 (13) Å, and Z=4 and V=1105.6 (3) Å3. And the compound 2 crystallizes in the orthorhombic crystal system and space group Pbca, with cell parameters a=16.5858 (5) Å, b=8.4947 (2) Å, c=23.1733 (7) Å, and Z=8 and V=3264.92 (16) Å3. The azepine ring of both molecules 1 and 2 adopts boat conformation with nitrogen atom showing maximum deviations of 0.483 (2) Å and 0.5025 (10) Å, respectively. The C–H⋯π short contacts were observed. The dihedral angle between fused benzene rings to the azepine motif is 47.1 (2)° for compound 1 and 52.59 (6)° for compound 2, respectively. The short contacts were analyzed and Hirshfeld surfaces computational method for both molecules revealed that the major contribution is from C⋯H and H⋯H intercontacts.
Highlights
Azepine derivatives have showed to be associated with different pharmacological activities such as antiviral, anticancer, anti-insecticidal, and vasopressin antagonist
Iminostilbene derivatives are found in montainine, coccinine, manthine, and pancracine alkaloids present in Haemanthus and Rhodophiala species [1]
They are the derivatives of drugs, such as carbamazepine [2], opipramol [3], and oxcarbazepine [4], which are used as anticonvulsants and antidepressants and in the treatment of epilepsy and trigeminal neuralgia [5]
Summary
Azepine derivatives have showed to be associated with different pharmacological activities such as antiviral, anticancer, anti-insecticidal, and vasopressin antagonist. Iminostilbene derivatives are found in montainine, coccinine, manthine, and pancracine alkaloids present in Haemanthus and Rhodophiala species [1]. They are the derivatives of drugs, such as carbamazepine [2], opipramol [3], and oxcarbazepine [4], which are used as anticonvulsants and antidepressants and in the treatment of epilepsy and trigeminal neuralgia [5]. Another compound, G32883, an iminostilbene derivative, shows effect on peripheral nerves [6]. The 11-phenyl-[b,e]-dibenzazepine compounds are proved to be novel antitumor compounds [9]
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